


Dear Dean

by TobytheWise



Series: Holiday Celebration [10]
Category: Supernatural
Genre: Coming Out, Fluff, Letters, Love Confessions, M/M, Marriage Proposal, sap, time jumps
Language: English
Status: Completed
Published: 2019-12-18
Updated: 2019-12-18
Packaged: 2021-02-26 12:01:01
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,199
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/21849316
Author URL: https://archiveofourown.org/users/TobytheWise/pseuds/TobytheWise
Summary: A series of letters from Castiel to Dean ranging from their first meeting to coming out to domestic married life.
Relationships: Castiel/Dean Winchester
Series: Holiday Celebration [10]
Series URL: https://archiveofourown.org/series/1559317
Comments: 18
Kudos: 95
Collections: The Destiel Fan Survey Favs Collection





	Dear Dean

**Author's Note:**

  * For [foxymoley](https://archiveofourown.org/users/foxymoley/gifts).



> This is written for one of my best friends, Foxy. I hope you enjoy <3

Dear Dean,  
My name is Castiel Novak and I am your neighbor. We have never talked or anything but I wanted to say thank you. You saw those bullies picking on me and you walked over and made them stop. I know I ran away but I was just so nervous and wanted to hide after that. So I thought I would write this letter and tell you how glad I am that you showed up.  
I don’t have a lot of friends because I’m new to this area. I know we go to the same school. So I was wondering, if you wanted to walk together to school in the morning? You are very nice and I thought maybe we could be friends?  
If you don’t want to that’s okay. I am kinda shy so I thought it would be easiest to just write you a letter. If you wanna walk to school, meet me by the fence between our houses in the morning.  
Thanks again,  
Castiel Novak

Dear Dean,  
It’s kinda funny if you think about it. The first interaction we had was through a letter, somewhat like this. I was shy and nervous and new. I’m still as shy, probably more nervous than I’ve been in my whole life, but no longer new.  
I was so scared, waiting at the fence for you, wondering whether or not you’d show up. But you were there with a giant smile and some extra breakfast for me. And look at us now! Best friends ever since.  
It’s our last day of high school. Through the years, you’ve become my very best friend, Dean. I can’t imagine life without you by my side.  
We’ve been through thick and thin. You saw me with my braces and I saw you through your goth phase. We’re just better together.  
Sorry I’m getting sappy. You know how I get when I’m nervous! And the thing I have to tell you could change everything.  
Next year we’re rooming together at college. And I can’t go through with that while I have this huge secret. I can’t put you in that position.  
If you read this and change your mind about me, I’ll understand. Just let me down easy, okay?  
Dean, I’m gay.  
Your friend (hopefully even now)  
Castiel

Dear Dean,  
I think I’m starting to see a pattern here. Every time I have something life changing to tell you, I write it out and then somehow find the courage to pass you the note. Some people would call me a coward. I’m not sure that I disagree with that assessment. I’m sorry I’m not brave enough to say this to your face. The mere thought of your rejection is too much for me to stomach.  
We’re about to graduate college and you keep asking me about my future, about our living situation, the big what’s next. And I keep pushing your questions away because I can’t answer them truthfully. Because the truth is, all I can think about is our future, and if we even have one.  
Over the years I’ve watched you date woman after woman, and for awhile that guy, Benny. I pretended to be happy when you were happy and I was always there so you could cry on my shoulder. But I can’t keep doing that, Dean. It hurts. It hurts to watch you with everybody but me.  
So here’s the truth. You asked me why I never date. You asked me where I wanna live next year. The honest truth is I never dated because I was too busy being in love with my best friend. And in a perfect world, once we graduate, I’d love to have a place with you. But not as roommates and best friend, but as partners.  
I know this is a lot and I’m sorry it’s through a letter. This is just like the time I told you I was gay. It sure feels the same from my end. My stomach is in knots and my palms are sweating. I really, really hope you don’t hate me.  
If you read this and don’t feel the same, it’s okay. You can pretend to have never read it and we can go back to being best friends. I’ll hide how I feel because being your friend is better than not having you in my life.  
But if you feel the same, I’ll be waiting at The Roadhouse tonight to take you on our first proper date. I even promise to pay. God, I hope I’ll see you tonight.  
I love you,  
Cas

Dear Dean,  
I assumed at this point it would just be wrong of me not to ask this in a letter. Letters have been our way of confessing things since we were little and I’m not going to stop now. I’ve got the biggest smile on my face as I write this, thinking back on all the things we’ve been through. From the day you saved me from bullies to last night when we’d celebrating our two year anniversary. Our night was filled with delicious dinner, sweet dessert and ended with us in bed, making slow, sweet love to each other. You make me happier than I’ve ever been.  
I still remember the night I waited for you at The Roadhouse, sweating through my dress shirt. You must have really loved me back then to look at me, a complete mess, and pull me into that toe curling kiss. Every day since, you remind me of why you love me. You make me feel treasured and precious. Dean, I love you. So fucking much.  
So now I’m going to be waiting. Because that’s apparently ‘our thing’. I write you a heartfelt letter, pouring out my heart and soul. And then I ask you to meet me somewhere, hoping with everything in me that you’ll show up.  
When life turns dark and dreary, I know you’ll always be there, lighting up my life. You literally make me a better version of myself, pushing me to be the best version of myself. You’re my best friend, my side-kick, my lover, and the one I want to raise kids with and eventually grow old with.  
So with all that, come outside. Because I’m outside, waiting on one knee so I can ask you to be my husband.  
I love you with all my heart,  
Cas (hopefully Winchester) 

Dear Dean,  
I promise this isn’t one of my confession letters. I just wanted to say I love you. I’ll miss you while I’m on my business trip but I know Jack will keep you company. (Plus I’m already planning how we’ll celebrate when I’m back home and yes, it has to do with those cuff you have hidden in your underwear drawer.)  
Sometimes it’s hard to believe how far we’ve come. From frightened children to husbands and dads. I wouldn’t have wanted to walk through life with anyone else by my side. I thank every deity that will listen for you, Dean.  
Your loving husband,  
Castiel Winchester  
PS I know you’re trying to be the ‘fun dad’ but please make sure Jack goes to bed on time. <3


End file.
